ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse

View Author Information
Center for Oceans and Human Health, Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United States
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United States
§ Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, United States
College of Pharmacy, Department of Medicinal Chemistry & Pharmacognosy and Center for Biomolecular Sciences, University of Illinois at Chicago, Chicago, Illinois 60612, United States
Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093, United States
Cite this: Chem. Rev. 2017, 117, 8, 5619–5674
Publication Date (Web):January 20, 2017
Copyright © 2017 American Chemical Society

    Article Views





    Other access options


    Abstract Image

    Naturally produced halogenated compounds are ubiquitous across all domains of life where they perform a multitude of biological functions and adopt a diversity of chemical structures. Accordingly, a diverse collection of enzyme catalysts to install and remove halogens from organic scaffolds has evolved in nature. Accounting for the different chemical properties of the four halogen atoms (fluorine, chlorine, bromine, and iodine) and the diversity and chemical reactivity of their organic substrates, enzymes performing biosynthetic and degradative halogenation chemistry utilize numerous mechanistic strategies involving oxidation, reduction, and substitution. Biosynthetic halogenation reactions range from simple aromatic substitutions to stereoselective C–H functionalizations on remote carbon centers and can initiate the formation of simple to complex ring structures. Dehalogenating enzymes, on the other hand, are best known for removing halogen atoms from man-made organohalogens, yet also function naturally, albeit rarely, in metabolic pathways. This review details the scope and mechanism of nature’s halogenation and dehalogenation enzymatic strategies, highlights gaps in our understanding, and posits where new advances in the field might arise in the near future.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.


    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 262 publications.

    1. Vyshnavi Vennelakanti, Mugyeom Jeon, Heather J. Kulik. How Do Differences in Electronic Structure Affect the Use of Vanadium Intermediates as Mimics in Nonheme Iron Hydroxylases?. Inorganic Chemistry 2024, Article ASAP.
    2. Tai L. Ng, Pamela A. Silver. Sustainable B12-Dependent Dehalogenation of Organohalides in E. coli. ACS Chemical Biology 2024, 19 (2) , 380-391.
    3. Audrey E. Yñigez-Gutierrez, Jennifer E. Wurm, Jordan T. Froese, Nicholas E. Rosenthal, Brian O. Bachmann. Characterization of Dichloroisoeverninic Acid Biosynthesis and Chemoenzymatic Synthesis of New Orthosomycins. ACS Chemical Biology 2024, 19 (2) , 526-535.
    4. Vyshnavi Vennelakanti, Grace L. Li, Heather J. Kulik. Why Nonheme Iron Halogenases Do Not Fluorinate C–H Bonds: A Computational Investigation. Inorganic Chemistry 2023, 62 (48) , 19758-19770.
    5. April L. Lukowski, Felix M. Hubert, Thuan-Ethan Ngo, Nicole E. Avalon, William H. Gerwick, Bradley S. Moore. Enzymatic Halogenation of Terminal Alkynes. Journal of the American Chemical Society 2023, 145 (34) , 18716-18721.
    6. Dibyendu Mondal, Harrison M. Snodgrass, Christian A. Gomez, Jared C. Lewis. Non-Native Site-Selective Enzyme Catalysis. Chemical Reviews 2023, 123 (16) , 10381-10431.
    7. Václav Zima, Mikuláš Vlk, Jiahao Wan, Josef Cvačka, František Tureček. Tracking Isomerizations of High-Energy Adenine Cation Radicals by UV–Vis Action Spectroscopy and Cyclic Ion Mobility Mass Spectrometry. The Journal of Physical Chemistry A 2023, 127 (28) , 5899-5913.
    8. Nguyet A. Nguyen, Vinayak Agarwal. A Leader-Guided Substrate Tolerant RiPP Brominase Allows Suzuki–Miyaura Cross-Coupling Reactions for Peptides and Proteins. Biochemistry 2023, 62 (12) , 1838-1843.
    9. Emilie F. Gérard, Thirakorn Mokkawes, Linus O. Johannissen, Jim Warwicker, Reynard R. Spiess, Christopher F. Blanford, Sam Hay, Derren J. Heyes, Sam P. de Visser. How Is Substrate Halogenation Triggered by the Vanadium Haloperoxidase from Curvularia inaequalis?. ACS Catalysis 2023, 13 (12) , 8247-8261.
    10. Yilin Chen, Wan-Qiu Liu, Xiao Zheng, Yifan Liu, Shengjie Ling, Jian Li. Cell-Free Biosynthesis of Lysine-Derived Unnatural Amino Acids with Chloro, Alkene, and Alkyne Groups. ACS Synthetic Biology 2023, 12 (4) , 1349-1357.
    11. Dong Zhang, Maoping Pu, Zhenzhong Liu, Yuqiao Zhou, Zhendong Yang, Xiaohua Liu, Yun-Dong Wu, Xiaoming Feng. Enantioselective anti-Dihalogenation of Electron-Deficient Olefin: A Triplet Halo-Radical Pylon Intermediate. Journal of the American Chemical Society 2023, 145 (8) , 4808-4818.
    12. Robert A. Singer, Sebastien Monfette, David Bernhardson, Sergei Tcyrulnikov, Aran K. Hubbell, Eric C. Hansen. Recent Advances in Nonprecious Metal Catalysis. Organic Process Research & Development 2022, 26 (12) , 3204-3215.
    13. Eva Pütz, Athanasios Gazanis, Nils Gert Keltsch, Olga Jegel, Felix Pfitzner, Ralf Heermann, Thomas A. Ternes, Wolfgang Tremel. Communication Breakdown: Into the Molecular Mechanism of Biofilm Inhibition by CeO2 Nanocrystal Enzyme Mimics and How It Can Be Exploited. ACS Nano 2022, 16 (10) , 16091-16108.
    14. Soumitra V. Athavale, Shilong Gao, Anuvab Das, Sharath Chandra Mallojjala, Edwin Alfonzo, Yueming Long, Jennifer S. Hirschi, Frances H. Arnold. Enzymatic Nitrogen Insertion into Unactivated C–H Bonds. Journal of the American Chemical Society 2022, 144 (41) , 19097-19105.
    15. Percival Yang-Ting Chen, Sanjoy Adak, Jonathan R. Chekan, David K. Liscombe, Akimasa Miyanaga, Peter Bernhardt, Stefan Diethelm, Elisha N. Fielding, Jonathan H. George, Zachary D. Miles, Lauren A. M. Murray, Taylor S. Steele, Jaclyn M. Winter, Joseph P. Noel, Bradley S. Moore. Structural Basis of Stereospecific Vanadium-Dependent Haloperoxidase Family Enzymes in Napyradiomycin Biosynthesis. Biochemistry 2022, 61 (17) , 1844-1852.
    16. Adriana Becerril, Ignacio Pérez-Victoria, Jesús M. Martín, Fernando Reyes, Jose A. Salas, Carmen Méndez. Biosynthesis of Largimycins in Streptomyces argillaceus Involves Transient β-Alkylation and Cryptic Halogenation Steps Unprecedented in the Leinamycin Family. ACS Chemical Biology 2022, 17 (8) , 2320-2331.
    17. Partha Pratim Sen, Vishal Jyoti Roy, Sudipta Raha Roy. Electrochemical Activation of the C–X Bond on Demand: Access to the Atom Economic Group Transfer Reaction Triggered by Noncovalent Interaction. The Journal of Organic Chemistry 2022, 87 (15) , 9551-9564.
    18. Aditya Nandy, Husain Adamji, David W. Kastner, Vyshnavi Vennelakanti, Azadeh Nazemi, Mingjie Liu, Heather J. Kulik. Using Computational Chemistry To Reveal Nature’s Blueprints for Single-Site Catalysis of C–H Activation. ACS Catalysis 2022, 12 (15) , 9281-9306.
    19. Emilie F. Gérard, Vishal Yadav, David P. Goldberg, Sam P. de Visser. What Drives Radical Halogenation versus Hydroxylation in Mononuclear Nonheme Iron Complexes? A Combined Experimental and Computational Study. Journal of the American Chemical Society 2022, 144 (24) , 10752-10767.
    20. Sanjoy Adak, April L. Lukowski, Rebecca J. B. Schäfer, Bradley S. Moore. From Tryptophan to Toxin: Nature’s Convergent Biosynthetic Strategy to Aetokthonotoxin. Journal of the American Chemical Society 2022, 144 (7) , 2861-2866.
    21. Oussama Yahiaoui, Lauren A. M. Murray, Fengyue Zhao, Bradley S. Moore, Kendall N. Houk, Fang Liu, Jonathan H. George. A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone. Organic Letters 2022, 24 (2) , 490-495.
    22. Jianxian Sun, Holly Barrett, David Ross Hall, Steven Kutarna, Xiaoqin Wu, Yan Wang, Hui Peng. Ecological Role of 6OH-BDE47: Is It a Chemical Offense Molecule Mediated by Enoyl-ACP Reductases?. Environmental Science & Technology 2022, 56 (1) , 451-459.
    23. Jing Zheng, Shane Antrobus, Wei Feng, Trevor N. Purdy, Bradley S. Moore, Isaac N. Pessah. Marine and Anthropogenic Bromopyrroles Alter Cellular Ca2+ Dynamics of Murine Cortical Neuronal Networks by Targeting the Ryanodine Receptor and Sarco/Endoplasmic Reticulum Ca2+-ATPase. Environmental Science & Technology 2021, 55 (23) , 16023-16033.
    24. Geoffrey W. Farley, Maxime A. Siegler, David P. Goldberg. Halogen Transfer to Carbon Radicals by High-Valent Iron Chloride and Iron Fluoride Corroles. Inorganic Chemistry 2021, 60 (22) , 17288-17302.
    25. Rimsha Mehmood, Vyshnavi Vennelakanti, Heather J. Kulik. Spectroscopically Guided Simulations Reveal Distinct Strategies for Positioning Substrates to Achieve Selectivity in Nonheme Fe(II)/α-Ketoglutarate-Dependent Halogenases. ACS Catalysis 2021, 11 (19) , 12394-12408.
    26. Nguyet A. Nguyen, Zhenjian Lin, Ipsita Mohanty, Neha Garg, Eric W. Schmidt, Vinayak Agarwal. An Obligate Peptidyl Brominase Underlies the Discovery of Highly Distributed Biosynthetic Gene Clusters in Marine Sponge Microbiomes. Journal of the American Chemical Society 2021, 143 (27) , 10221-10231.
    27. Mengting Liu, Masao Ohashi, Yiu-Sun Hung, Kirstin Scherlach, Kenji Watanabe, Christian Hertweck, Yi Tang. AoiQ Catalyzes Geminal Dichlorination of 1,3-Diketone Natural Products. Journal of the American Chemical Society 2021, 143 (19) , 7267-7271.
    28. Guodong Zhao, Eryu Wang, Rongbiao Tong. From Reactive Oxygen Species to Reactive Brominating Species: Fenton Chemistry for Oxidative Bromination. ACS Sustainable Chemistry & Engineering 2021, 9 (17) , 6118-6125.
    29. Jonathan H. George. Biomimetic Dearomatization Strategies in the Total Synthesis of Meroterpenoid Natural Products. Accounts of Chemical Research 2021, 54 (8) , 1843-1855.
    30. Andrew Jordan, Patrick Stoy, Helen F. Sneddon. Chlorinated Solvents: Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry. Chemical Reviews 2021, 121 (3) , 1582-1622.
    31. Yu Fu, Jian Huang, Yuzhou Wu, Xiaohong Liu, Fangrui Zhong, Jiangyun Wang. Biocatalytic Cross-Coupling of Aryl Halides with a Genetically Engineered Photosensitizer Artificial Dehalogenase. Journal of the American Chemical Society 2021, 143 (2) , 617-622.
    32. Katsuhiko Moriyama, Masako Kuramochi, Seiji Tsuzuki, Kozo Fujii, Takeshi Morita. Nitroxyl Catalysts for Six-Membered Ring Bromolactonization and Intermolecular Bromoesterification of Alkenes with Carboxylic Acids. Organic Letters 2021, 23 (2) , 268-273.
    33. M. Qadri E. Mubarak, Emilie F. Gérard, Christopher F. Blanford, Sam Hay, Sam P. de Visser. How Do Vanadium Chloroperoxidases Generate Hypochlorite from Hydrogen Peroxide and Chloride? A Computational Study. ACS Catalysis 2020, 10 (23) , 14067-14079.
    34. Hem R. Thapa, Zhenjian Lin, Dongqi Yi, Jennifer E. Smith, Eric W. Schmidt, Vinayak Agarwal. Genetic and Biochemical Reconstitution of Bromoform Biosynthesis in Asparagopsis Lends Insights into Seaweed Reactive Oxygen Species Enzymology. ACS Chemical Biology 2020, 15 (6) , 1662-1670.
    35. Terry F. Bidleman, Agneta Andersson, Peter Haglund, Mats Tysklind. Will Climate Change Influence Production and Environmental Pathways of Halogenated Natural Products?. Environmental Science & Technology 2020, 54 (11) , 6468-6485.
    36. Huijuan Guo, Jan W. Schwitalla, René Benndorf, Martin Baunach, Christoph Steinbeck, Helmar Görls, Z. Wilhelm de Beer, Lars Regestein, Christine Beemelmanns. Gene Cluster Activation in a Bacterial Symbiont Leads to Halogenated Angucyclic Maduralactomycins and Spirocyclic Actinospirols. Organic Letters 2020, 22 (7) , 2634-2638.
    37. Bin Tan, Qingbo Zhang, Yiguang Zhu, Hongbo Jin, Liping Zhang, Siqiang Chen, Changsheng Zhang. Deciphering Biosynthetic Enzymes Leading to 4-Chloro-6-Methyl-5,7-Dihydroxyphenylglycine, a Non-Proteinogenic Amino Acid in Totopotensamides. ACS Chemical Biology 2020, 15 (3) , 766-773.
    38. Paulo R. M. Pereira, Jéssica de O. Araújo, José Rogério A. Silva, Cláudio N. Alves, Jerônimo Lameira, Anderson H. Lima. Exploring Chloride Selectivity and Halogenase Regioselectivity of the SalL Enzyme through Quantum Mechanical/Molecular Mechanical Modeling. Journal of Chemical Information and Modeling 2020, 60 (2) , 738-746.
    39. Sabine Duewel, Luca Schmermund, Tabea Faber, Klaus Harms, Vasundara Srinivasan, Eric Meggers, Sabrina Hoebenreich. Directed Evolution of an FeII-Dependent Halogenase for Asymmetric C(sp3)–H Chlorination. ACS Catalysis 2020, 10 (2) , 1272-1277.
    40. Jonathan R. Chekan, Ga Young Lee, Abrahim El Gamal, Trevor N. Purdy, K. N. Houk, Bradley S. Moore. Bacterial Tetrabromopyrrole Debrominase Shares a Reductive Dehalogenation Strategy with Human Thyroid Deiodinase. Biochemistry 2019, 58 (52) , 5329-5338.
    41. Rentai Song, Haixia Shi, Jing Zhu, Haoxin Wang, Yuemao Shen. A Single-Component Flavoenzyme Catalyzed Regioselective Halogenation of Pyrone in the Biosynthesis of Venemycins. ACS Chemical Biology 2019, 14 (12) , 2533-2537.
    42. Fabian Panter, Ronald Garcia, Angela Thewes, Nestor Zaburannyi, Boyke Bunk, Jörg Overmann, Mary V. Gutierrez, Daniel Krug, Rolf Müller. Production of a Dibrominated Aromatic Secondary Metabolite by a Planctomycete Implies Complex Interaction with a Macroalgal Host. ACS Chemical Biology 2019, 14 (12) , 2713-2719.
    43. Brian F. Fisher, Harrison M. Snodgrass, Krysten A. Jones, Mary C. Andorfer, Jared C. Lewis. Site-Selective C–H Halogenation Using Flavin-Dependent Halogenases Identified via Family-Wide Activity Profiling. ACS Central Science 2019, 5 (11) , 1844-1856.
    44. Joonwon Kim, Jeongchan Lee, Pyung-Gang Lee, Eun-Jung Kim, Wolfgang Kroutil, Byung-gee Kim. Elucidating Cysteine-Assisted Synthesis of Indirubin by a Flavin-Containing Monooxygenase. ACS Catalysis 2019, 9 (10) , 9539-9544.
    45. Yadagiri Kommagalla, Naoto Chatani. Cobalt-Catalyzed C–H Iodination of Aromatic Amides with Molecular Iodine through the Use of a 2-Aminophenyloxazoline-Based Bidentate-Chelation System. Organic Letters 2019, 21 (15) , 5971-5976.
    46. Paul O. Guillen, Karla B. Jaramillo, Laurence Jennings, Grégory Genta-Jouve, Mercedes de la Cruz, Bastien Cautain, Fernando Reyes, Jenny Rodríguez, Olivier P. Thomas. Halogenated Tyrosine Derivatives from the Tropical Eastern Pacific Zoantharians Antipathozoanthus hickmani and Parazoanthus darwini. Journal of Natural Products 2019, 82 (5) , 1354-1360.
    47. Sanjoy Adak, Tadhg P. Begley. Hexachlorobenzene Catabolism Involves a Nucleophilic Aromatic Substitution and Flavin-N5-Oxide Formation. Biochemistry 2019, 58 (9) , 1181-1183.
    48. Parthasarathy Gandeepan, Thomas Müller, Daniel Zell, Gianpiero Cera, Svenja Warratz, Lutz Ackermann. 3d Transition Metals for C–H Activation. Chemical Reviews 2019, 119 (4) , 2192-2452.
    49. Margarida Costa, Ivo E. Sampaio-Dias, Raquel Castelo-Branco, Hugo Scharfenstein, Roberta Rezende de Castro, Artur Silva, Maria Paula C. Schneider, Maria João Araújo, Rosário Martins, Valentina F. Domingues, Fátima Nogueira, Vera Camões, Vitor M. Vasconcelos, Pedro N. Leão. Structure of Hierridin C, Synthesis of Hierridins B and C, and Evidence for Prevalent Alkylresorcinol Biosynthesis in Picocyanobacteria. Journal of Natural Products 2019, 82 (2) , 393-402.
    50. Shaun M. K. McKinnie, Zachary D. Miles, Peter A. Jordan, Takayoshi Awakawa, Henry P. Pepper, Lauren A. M. Murray, Jonathan H. George, Bradley S. Moore. Total Enzyme Syntheses of Napyradiomycins A1 and B1. Journal of the American Chemical Society 2018, 140 (51) , 17840-17845.
    51. Zuodong Sun, Steven E. Rokita. Toward a Halophenol Dehalogenase from Iodotyrosine Deiodinase via Computational Design. ACS Catalysis 2018, 8 (12) , 11783-11793.
    52. Danielle R. Monteverde, Jason B. Sylvan, Christopher Suffridge, J. Jotautas Baronas, Erin Fichot, Jed Fuhrman, William Berelson, Sergio A. Sañudo-Wilhelmy. Distribution of Extracellular Flavins in a Coastal Marine Basin and Their Relationship to Redox Gradients and Microbial Community Members. Environmental Science & Technology 2018, 52 (21) , 12265-12274.
    53. Fraser A. Collins, Karl Fisher, Karl A. P. Payne, Samantha Gaytan Mondragon, Stephen E. J. Rigby, David Leys. NADPH-Driven Organohalide Reduction by a Nonrespiratory Reductive Dehalogenase. Biochemistry 2018, 57 (25) , 3493-3502.
    54. Celso Almeida, Ignacio Pérez-Victoria, Víctor González-Menéndez, Nuria de Pedro, Jesús Martín, Gloria Crespo, Thomas Mackenzie, Bastien Cautain, Fernando Reyes, Francisca Vicente, Olga Genilloud. Non-geminal Aliphatic Dihalogenation Pattern in Dichlorinated Diaporthins from Hamigera fusca NRRL 35721. Journal of Natural Products 2018, 81 (6) , 1488-1492.
    55. Jing Zheng, Shaun M. K. McKinnie, Abrahim El Gamal, Wei Feng, Yao Dong, Vinayak Agarwal, William Fenical, Abdhesh Kumar, Zhengyu Cao, Bradley S. Moore, Isaac N. Pessah. Organohalogens Naturally Biosynthesized in Marine Environments and Produced as Disinfection Byproducts Alter Sarco/Endoplasmic Reticulum Ca2+ Dynamics. Environmental Science & Technology 2018, 52 (9) , 5469-5478.
    56. Yi Zhu, Jianlin Han, Jiandong Wang, Norio Shibata, Mikiko Sodeoka, Vadim A. Soloshonok, Jaime A. S. Coelho, F. Dean Toste. Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs. Chemical Reviews 2018, 118 (7) , 3887-3964.
    57. Denghu Chang, Rong Zhao, Congyin Wei, Yuan Yao, Yang Liu, Lei Shi. Sulfonamide-Directed Chemo- and Site-Selective Oxidative Halogenation/Amination Using Halogenating Reagents Generated in Situ from Cyclic Diacyl Peroxides. The Journal of Organic Chemistry 2018, 83 (6) , 3305-3315.
    58. Elvira Romero, J. Rubén Gómez Castellanos, Giovanni Gadda, Marco W. Fraaije, Andrea Mattevi. Same Substrate, Many Reactions: Oxygen Activation in Flavoenzymes. Chemical Reviews 2018, 118 (4) , 1742-1769.
    59. Tatyana D. Grayfer, Pascal Retailleau, Robert H. Dodd, Joëlle Dubois, and Kevin Cariou . Chemodivergent, Tunable, and Selective Iodine(III)-Mediated Bromo-Functionalizations of Polyprenoids. Organic Letters 2017, 19 (18) , 4766-4769.
    60. David K. Romney, Javier Murciano-Calles, Jöri E. Wehrmüller, Frances H. Arnold. Unlocking Reactivity of TrpB: A General Biocatalytic Platform for Synthesis of Tryptophan Analogues. Journal of the American Chemical Society 2017, 139 (31) , 10769-10776.
    61. Wilfred A. van der Donk . Introduction: Unusual Enzymology in Natural Product Synthesis. Chemical Reviews 2017, 117 (8) , 5223-5225.
    62. GuangRong Peh, Terence Tay, Lee Ling Tan, Elaine Tiong, Jiawu Bi, Yi Ling Goh, Suming Ye, Fu Lin, Cheryl Jia Xin Tan, Yong Zi Tan, Joel Wong, Huimin Zhao, Fong Tian Wong, Ee Lui Ang, Yee Hwee Lim. Site-selective chlorination of pyrrolic heterocycles by flavin dependent enzyme PrnC. Communications Chemistry 2024, 7 (1)
    63. Nguyet A. Nguyen, F. N. U. Vidya, Neela H. Yennawar, Hongwei Wu, Andrew C. McShan, Vinayak Agarwal. Disordered regions in proteusin peptides guide post-translational modification by a flavin-dependent RiPP brominase. Nature Communications 2024, 15 (1)
    64. Constanze Kuhlisch, Adva Shemi, Noa Barak-Gavish, Daniella Schatz, Assaf Vardi. Algal blooms in the ocean: hot spots for chemically mediated microbial interactions. Nature Reviews Microbiology 2024, 22 (3) , 138-154.
    65. Keisuke Tokushige, Takumi Abe. On Demand Synthesis of C3−N1’ Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (±)‐Rivularin A. Chemistry – A European Journal 2024, 30 (11)
    66. Qiaoyu Zhang, Qianqian Chen, Sason Shaik, Binju Wang. Flavin‐N5OOH Functions as both a Powerful Nucleophile and a Base in the Superfamily of Flavoenzymes. Angewandte Chemie 2024, 278
    67. Yuhua Jiang, Ahram Kim, Cahmlo Olive, Jared C. Lewis. Selective C−H Halogenation of Alkenes and Alkynes Using Flavin‐Dependent Halogenases. Angewandte Chemie International Edition 2024, 47
    68. Yuhua Jiang, Ahram Kim, Cahmlo Olive, Jared C. Lewis. Selective C−H Halogenation of Alkenes and Alkynes Using Flavin‐Dependent Halogenases. Angewandte Chemie 2024, 47
    69. Zequan Huang, Dong Liu, Shang Chen, Jinwei Ren, Chenghai Gao, Zhiyong Li, Aili Fan, Wenhan Lin. Brominated Depsidones with Antibacterial Effects from a Deep-Sea-Derived Fungus Spiromastix sp.. Marine Drugs 2024, 22 (2) , 78.
    70. Nathaniel R. Glasser, Dongtao Cui, Douglas D. Risser, C. Denise Okafor, Emily P. Balskus. Accelerating the discovery of alkyl halide-derived natural products using halide depletion. Nature Chemistry 2024, 16 (2) , 173-182.
    71. Qiaoyu zhang, Qianqian chen, Sason shaik, Binju Wang. Flavin‐N5OOH Functions as both a Powerful Nucleophile and a Base in the Superfamily of Flavoenzymes. Angewandte Chemie International Edition 2024,
    72. Juan Chen, Bo Zhang, Chao Wang, Peifang Wang, Ge Cui, Han Gao, Bingbing Feng, Jingjing Zhang. Insight into the enhancement effect of humic acid on microbial degradation of triclosan in anaerobic sediments. Journal of Hazardous Materials 2024, 461 , 132549.
    73. Fabiola Muro-Villanueva, Ryan S. Nett. Emerging functions within the enzyme families of plant alkaloid biosynthesis. Phytochemistry Reviews 2023, 117
    74. Aisaraphon Phintha, Pimchai Chaiyen. Unifying and versatile features of flavin-dependent monooxygenases: Diverse catalysis by a common C4a-(hydro)peroxyflavin. Journal of Biological Chemistry 2023, 299 (12) , 105413.
    75. Paul M. D'Agostino. Highlights of biosynthetic enzymes and natural products from symbiotic cyanobacteria. Natural Product Reports 2023, 40 (11) , 1701-1717.
    76. Jiaqiong Sun, Yunliang Guo, Jiuli Xia, Guangfan Zheng, Qian Zhang. Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N–X (Halogen) Reagents. Molecules 2023, 28 (21) , 7420.
    77. Valery M. Dembitsky. Steroids Bearing Heteroatom as Potential Drugs for Medicine. Biomedicines 2023, 11 (10) , 2698.
    78. Bo Zhao, Jiali Wang, Na Sun, Chunguang Liu. Low concentration of bromide ions improves sulfadiazine phytoremoval and attenuates its phytotoxicity. Science of The Total Environment 2023, 893 , 164857.
    79. Huaran Zhang, Yuting Huang, Yingjie Tang, Dekun Kong, Yi Zou. Genome mining of multi-substituted alkylresorcinols from a hybrid highly reducing- and type III- polyketide pathway. Chinese Chemical Letters 2023, 34 , 108968.
    80. Vitor S.C. de Andrade, Marcio C.S. de Mattos. Oxidative Chlorination: A Sustainable Alternative for the Preparation of Chloroarenes. Current Green Chemistry 2023, 10 (2) , 143-159.
    81. Yuhua Jiang, Jared C. Lewis. Asymmetric catalysis by flavin‐dependent halogenases. Chirality 2023, 35 (8) , 452-460.
    82. Bastien Cochereau, Yoran Le Strat, Qiaolin Ji, Audrey Pawtowski, Ludovic Delage, Amélie Weill, Lisa Mazéas, Cécile Hervé, Gaëtan Burgaud, Nina Gunde-Cimerman, Yves François Pouchus, Nathalie Demont-Caulet, Catherine Roullier, Laurence Meslet-Cladiere. Heterologous Expression and Biochemical Characterization of a New Chloroperoxidase Isolated from the Deep-Sea Hydrothermal Vent Black Yeast Hortaea werneckii UBOCC-A-208029. Marine Biotechnology 2023, 25 (4) , 519-536.
    83. Bastien Cochereau, Thibaut Robiou du Pont, Yves François Pouchus, Deniz Tasdemir, Laurence Meslet-Cladière, Catherine Roullier. Enzymatic bromination of marine fungal extracts for enhancement of chemical diversity. Biocatalysis and Agricultural Biotechnology 2023, 51 , 102786.
    84. Jinyan Zhang, Peng Wu, Xuan Zhang, Binju Wang. Coordination Dynamics of Iron is a Key Player in the Catalysis of Non‐heme Enzymes. ChemBioChem 2023, 24 (14)
    85. Hejie Qin, Tanjie Zha, Kun Qian, Yuankui Sun, Xiaohong Guan, Chuncheng Chen. Efficient full dechlorination of chlorinated ethenes on single enzyme-like Co−N4 sites in nitrogen-doped carbons. Applied Catalysis B: Environmental 2023, 328 , 122459.
    86. Simon Gäfe, Hartmut H. Niemann. Structural basis of regioselective tryptophan dibromination by the single-component flavin-dependent halogenase AetF. Acta Crystallographica Section D Structural Biology 2023, 79 (7) , 596-609.
    87. GuangRong Peh, Gregory A. Gunawan, Terence Tay, Elaine Tiong, Lee Ling Tan, Shimin Jiang, Yi Ling Goh, Suming Ye, Joel Wong, Christopher J. Brown, Huimin Zhao, Ee Lui Ang, Fong Tian Wong, Yee Hwee Lim. Further Characterization of Fungal Halogenase RadH and Its Homologs. Biomolecules 2023, 13 (7) , 1081.
    88. Pola Łomża, Tomasz Krucoń, Agnieszka Tabernacka. Potential of Microbial Communities to Perform Dehalogenation Processes in Natural and Anthropogenically Modified Environments—A Metagenomic Study. Microorganisms 2023, 11 (7) , 1702.
    89. Yu Fu, Xiaohong Liu, Yan Xia, Xuzhen Guo, Juan Guo, Junshuai Zhang, Weining Zhao, Yuzhou Wu, Jiangyun Wang, Fangrui Zhong. Whole-cell-catalyzed hydrogenation/deuteration of aryl halides with a genetically repurposed photodehalogenase. Chem 2023, 9 (7) , 1897-1909.
    90. Zhijun Tang, Bo Pang, Chang Liu, Shengjie Guo, Xudong Qu, Wen Liu. Formation and Loading of a (2 S )‐2‐Ethylmalonamyl Starter Unit in the Assembly Line of Polyketide‐Nonribosomal Peptide Hybrid Sanglifehrin A. Angewandte Chemie 2023, 135 (23)
    91. Zhijun Tang, Bo Pang, Chang Liu, Shengjie Guo, Xudong Qu, Wen Liu. Formation and Loading of a (2 S )‐2‐Ethylmalonamyl Starter Unit in the Assembly Line of Polyketide‐Nonribosomal Peptide Hybrid Sanglifehrin A. Angewandte Chemie International Edition 2023, 62 (23)
    92. Jia‐jing Liang, Hang Li. Fusion Enzymes Involved in Biosynthetic Tailoring Reactions in Fungi. ChemBioChem 2023, 24 (11)
    93. Kensuke Kaneko, Daiki Kobayashi, Shiro Masaki, Kenji Washio, Masaaki Morikawa, Tatsufumi Okino. Gene cloning and characterization of a vanadium-dependent bromoperoxidase from the red alga Laurencia saitoi, a producer of brominated diterpenoids and triterpenoids. Journal of Applied Phycology 2023, 35 (3) , 1443-1452.
    94. Eimear Hegarty, Johannes Büchler, Rebecca M. Buller. Halogenases for the synthesis of small molecules. Current Opinion in Green and Sustainable Chemistry 2023, 41 , 100784.
    95. Pedro N. Leão, Teresa P. Martins, Kathleen Abt, João P. A. Reis, Sandra Figueiredo, Raquel Castelo-Branco, Sara Freitas. Incorporation and modification of fatty acids in cyanobacterial natural products biosynthesis. Chemical Communications 2023, 59 (30) , 4436-4446.
    96. Tianhao Yu, Haiyang Cui, Jianan Canal Li, Yunan Luo, Guangde Jiang, Huimin Zhao. Enzyme function prediction using contrastive learning. Science 2023, 379 (6639) , 1358-1363.
    97. Elijah N. Kissman, Monica E. Neugebauer, Kiera H. Sumida, Cameron V. Swenson, Nicholas A. Sambold, Jorge A. Marchand, Douglas C. Millar, Michelle C. Y. Chang. Biocatalytic control of site-selectivity and chain length-selectivity in radical amino acid halogenases. Proceedings of the National Academy of Sciences 2023, 120 (12)
    98. Eva Pütz, Ina Tutzschky, Hajo Frerichs, Wolfgang Tremel. In situ generation of H 2 O 2 using CaO 2 as peroxide storage depot for haloperoxidase mimicry with surface-tailored Bi-doped mesoporous CeO 2 nanozymes. Nanoscale 2023, 15 (11) , 5209-5218.
    99. Niamh M. O’Boyle, Jean-Jacques Helesbeux, Mary J. Meegan, Astrid Sasse, Elizabeth O’Shaughnessy, Alina Qaisar, Aoife Clancy, Florence McCarthy, Pascal Marchand. 30th Annual GP2A Medicinal Chemistry Conference. Pharmaceuticals 2023, 16 (3) , 432.
    100. Fleurdeliz Maglangit, Hai Deng. Cell Factory for Phenylnaphthacenoid Polyketide Production. SynBio 2023, 1 (1) , 89-102.
    Load more citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect